N-(4-Chlorophenyl)-2-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-3-carboxamide → N-(4-Chlorophenyl)-2-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-3-methylamine

HRID 397549Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[N:13][CH:14]=[CH:15][CH:16]=2)=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:11]2[C:12]([NH:17][CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of N-(4-chlorophenyl)-2-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-3-carboxamide (25 mg, 0.059 mmol) in THF (1 mL) was treated with lithium aluminum hydride (1.0 M in THF, 0.21 mL, 0.21 mmol). The mixture was heated at 65° C. for 4 days, cooled, diluted with methanol (5 mL), and loaded onto an SCX ion exchange resin. The resin was eluted with methanol followed by 2 N NH3 in methanol and fractions containing the desired material were concentrated. The residue was triturated with EtOAc, yielding 15 mg (62%) of the title compound.

Workup

temperaturecooled
washThe resin was eluted with methanol
additioncontaining the desired material
concentrationwere concentrated
customThe residue was triturated with EtOAc

Sources & evidence

ORD record: ord-db2b6b42285e4d6cb1eec9619fe8d06a
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610704B1

Reaction notes

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